Hydroxamic acid derivatives

ABSTRACT

The invention relates to novel hydroxamic acid derivatives, to a plurality of processes for their preparation and to their use as pesticides.

This application was filed under 35 U.S.C. 371, and is the U.S. NationalStage of PCT/EP00/10918, filed 6, Nov. 2000.

The invention relates to novel hydroxamic acid derivatives to aplurality of processes for their preparation and to their use aspesticides.

Certain hydroxamic acid derivatives having a similar substitutionpattern, and their fungicidal action, are already known (compare, forexample, WO 95-20570)). However, in particular at low application ratesand concentrations, the activity of these prior-art compounds is notentirely satisfactory in all areas of use.

This invention, accordingly, provides the novel hydroxamic acidderivatives of the general formula (I)

in which

Z represents in each case substituted or unsubstituted cycloalkyl, arylor heterocyclyl,

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represent hydrogen, halogen, cyano, nitro, in each caseoptionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinylor alkylsulfonyl,

R¹ represents hydrogen or alkyl and

R² represents hydrogen, alkyl, alkylcarbonyl, alkoxycarbonyl orarylcarbonyl.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkanediyl, alkenyl or alkinyl, are in each casestraight-chain or branched, including in combination with heteroatoms,such as, for example, in alkoxy, alkylthio or alkylamino. Unless statedotherwise, preference is given to hydrocarbon chains having 1 to 6carbon atoms.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, suchas, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferablyphenyl or naphthyl, in particular phenyl, which may optionally also befuzed to further aliphatic or heterocyclic rings. Thus, aryl alsorepresents tetralinyl, indolyl or benzofuranyl, for example; however,the point of attachment is at the phenyl moiety.

Heterocyclyl represents saturated or unsaturated, and also aromatic,cyclic compounds in which at least one ring member is a heteroatom, i.e.an atom different from carbon. If the ring contains a plurality ofheteroatoms, these can be identical or different. Preferred heteroatomsare oxygen, nitrogen or sulfur. If the ring contains a plurality ofoxygen atoms, these are not adjacent. The cyclic compounds mayoptionally form a polycyclic ring system with other carbocyclic orheterocyclic fuzed-on or bridged rings. Preference is given to mono- orbicyclic ring systems, in particular to mono- or bicyclic aromatic ringsystems.

Cycloalkyl represents saturated carbocyclic cyclic compounds which mayoptionally form a polycyclic ring system with other carbocyclic fuzed-onor bridged rings.

A polycyclic ring system may be attached to a heterocyclic ring or afuzed-on carbocyclic ring. The heterocyclyl radical described in thismanner may also be mono- or polysubstituted, preferably by methyl,ethyl, halogen or chlorine. Preference is given to mono- or bicyclicring systems, in particular to mono- or bicyclic ring systems.

Halogenoalkoxy represents partially or fully halogenated alkoxy. In thecase of polyhalogenated halogenoalkoxy, the halogen atoms can beidentical or different. Preferred halogen atoms are fluorine and, inparticular, chlorine. If the halogenoalkoxy carries other substituents,the maximum possible number of halogen atoms is reduced to the differentfree valencies.

Halogenoalkyl represents partially or fully halogenated alkyl. In thecase of polyhalogenated halogenoalkyl, the halogen atoms can beidentical or different.

Preferred halogen atoms are fluorine and chlorine, in particularfluorine. If the halogenoalkyl carries other substituents, the maximumpossible number of halogen atoms is reduced to the remaining freevalencies.

Furthermore, it has been found that the novel hydroxamic acidderivatives of the general formula (I) are obtained when

a) carboxylic acid derivatives of the formula (II)

in which

L¹, L², L³, L⁴ and Z are as defined above and

X¹ represents halogen, are reacted with a substituted or unsubstitutedhydroxylamine derivative of the general formula (III)

in which

R¹ and R² are as defined above,

if appropriate in the presence of a diluent and if appropriate in thepresence of an acid acceptor, or when

b) compounds of the general formula (I) where R² is hydrogen are reactedwith a halogen compound of the general formula (IV)

X²—R²′  (IV)

in which

R²′ represents alkyl, alkylcarbonyl, alkoxycarbonyl or arylcarbonyl and

X² represents halogen, if appropriate in the presence of a diluent, ifappropriate in the presence of an acid acceptor.

Finally, it has been found that the novel hydroxamic acid derivatives ofthe general formula (I) have very strong very strong activity againstpests of plants.

If appropriate, the compounds according to the invention can be presentas mixtures of different possible isomeric forms, in particular ofstereoisomers, such as, for example, E and Z. What is claimed are boththe E and the Z isomers, and also any mixtures of these isomers.

The invention preferably provides compounds of the formula (I) in which

Z represents cycloalkyl having 3 to 7 carbon atoms which is optionallymono- to disubstituted by halogen, alkyl or hydroxyl;

represents heterocyclyl having 3 to 7 ring members which is optionallysubstituted by alkyl having 1 to 4 carbon atoms;

or represents phenyl or naphthyl, each of which is optionally mono- totetrasubstituted by identical or different substituents, where thepossible substituents are preferably selected from the list below:

halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl,thiocarbamoyl;

in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl,alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio,alkylsulfinyl or alkylsulfonyl having in each case 1 to 8 carbon atoms;

in each case straight-chain or branched alkenyl or alkenyloxy having ineach case 2 to 6 carbon atoms;

in each case straight-chain or branched halogenoalkyl, halogenoalkoxy,halogenoalkylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl havingin each case 1 to 6 carbon atoms and 1 to 13 identical or differenthalogen atoms;

in each case straight-chain or branched halogenoalkenyl orhalogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11identical or different halogen atoms;

in each case straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy,alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in thehydrocarbon chains in question;

cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms;

in each case doubly attached alkylene having 3 to 4 carbon atoms,oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2carbon atoms, each of which radicals is optionally mono- totetrasubstituted by identical or different radicals from the groupconsisting of fluorine, chlorine, oxo, methyl, trifluoromethyl andethyl;

or a grouping

in which

A¹ represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms orcycloalkyl having 1 to 6 carbon atoms and

A² represents hydroxyl, amino, methylamino, phenyl, benzyl or representsin each case optionally cyano-, hydroxyl-, alkoxy-, alkylthio-,alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having1 to 4 carbon atoms, or represents alkenyloxy or alkinyloxy having ineach case 2 to 4 carbon atoms, and also phenyl, phenoxy, phenylthio,benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl,phenylalkyloxy, phenylalkylthio, or heterocyclylalkyl, having in eachcase 1 to 3 carbon atoms in the alkyl moieties in question, each ofwhich radicals is optionally mono- to trisubstituted in the cyclicmoiety by halogen and/or straight-chain or branched alkyl or alkoxyhaving 1 to 4 carbon atoms,

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represents hydrogen, halogen, cyano, nitro, or alkyl,alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having in each case 1to 6 carbon atoms, each of which radicals is optionally substituted by 1to 5 halogen atoms,

R¹ represents hydrogen or alkyl and

R² represents hydrogen, alkyl, alkylcarbonyl, alkoxycarbonyl orarylcarbonyl.

The invention relates in particular to compounds of the formula (I) inwhich

Z represents cyclopentyl or cyclohexyl, each of which is optionallymono- to disubstituted by fluorine, chlorine, methyl, ethyl or hydroxyl;

represents furyl, pyridyl or thienyl which is optionally substituted bymethyl or ethyl;

or represents phenyl or naphthyl, each of which is optionally mono- totetrasubstituted by identical or different substituents, where thepossible substituents are preferably selected from the list below:

fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl,formyl, carboxyl, carbamoyl, thiocarbamoyl,

methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-,neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-,4-, 5-(2-methylpentyl), 1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-,3-, 4-(2,2-dimetylbutyl), 1-, 2-(2,3-dimethylbutyl), hydroxymethyl,hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl,

methoxy, ethoxy, n- or i-propoxy, methoxymethyl, ethoxymethyl,

methylthio, ethylthio, n- or i-propylthio, methylsulfinyl,ethylsulfinyl, methyl-sulfonyl or ethylsulfonyl, methylthiomethyl,ethylthiomethyl,

vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy,allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy;

trifluoromethyl, trifluoroethyl,

difluoromethoxy, trifluoromethoxy, difluorochloromethoxy,trifluoroethoxy, difluoromethylthio, trifluoromethylthio,difluorochloromethylthio, trifluoromethylsulfinyl ortrifluoromethylsulfonyl,

methylamino, ethylamino, n- or i-propylamino, dimethylamino,diethylamino,

acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl,ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylaminocarbonyl,acryloyl, propioloyl,

cyclopentyl, cyclohexyl,

in each case doubly attached propanediyl, ethyleneoxy, methylenedioxy,ethylenedioxy, each of which is optionally mono- to tetrasubstituted byidentical or different substituents from the group consisting offluorine, chlorine, oxo, methyl and trifluoromethyl

or a grouping

where

A¹ represents hydrogen, methyl or hydroxyl and

A² represents hydroxyl, methoxy, ethoxy, amino, methylamino, phenyl,benzyl or hydroxyethyl, and also

phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl,phenylethyl, phenylpropyl, benzyloxy, benzylthio,5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl,benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl,oxadiazolyl, each of which is optionally mono- to trisubstituted in thecyclic moiety by halogen and/or straight-chain or branched alkyl oralkoxy having 1 to 4 carbon atoms,

L¹, L², L³ and L⁴ are identical or different and independently of oneanother each represent hydrogen, methyl, ethyl, n- or i-propyl, n-, i-,s- or t-butyl,

R¹ represents hydrogen or alkyl,

R² represents hydrogen, alkyl, alkylcarbonyl, alkoxycarbonyl orarylcarbonyl.

In a very particularly preferred group of compounds, Z representsoptionally substituted phenyl.

Particular preference is given to compounds of the formula (I) in whichR¹ represents hydrogen and, in particular, methyl.

Particular preference is given to compounds of the formula (I) in whichZ represents optionally substituted phenyl, where the substituents arepreferably selected from the list below: halogen, cyano, in each casestraight-chain or branched alkyl, alkylthio, alkylthioalkyl,halogenoalkyl, halogenothioalkyl.

In a further very particularly preferred group of compounds

L¹, L² and L³ represent hydrogen and

L⁴ represents hydrogen or represents methyl.

The invention relates particularly preferably to compounds of theformula (I) in which

Z represents phenyl which is in each case optionally mono- totrisubstituted by identical or different substituents, where thesubstituents are selected from the list below: fluorine, chlorine,C₁-C₄-alkyl or cyano,

L¹, L², L³ and L⁴ represent hydrogen,

R¹ represents C₁-C₄-alkyl, and

R² represents hydrogen or methyl.

The general or preferred radical definitions given above apply both tothe end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation.

The specific radical definitions given in the combinations or preferredcombinations of radicals in question for these radicals are,independently of the combination of radicals given in each case, alsoreplaced by any radical definitions of other preferred ranges.

The formula (II) provides a general definition of the carboxylic acidderivatives required as starting materials for carrying out the processa) according to the invention. In this formula (II), L¹, L², L³, L⁴ andZ preferably or in particular have those meanings which have alreadybeen mentioned in connection with the description of the compounds ofthe formula (I) according to the invention as being preferred or asbeing particularly preferred for L¹, L², L³, L⁴ and Z. X¹ representshalogen, preferably chlorine.

The starting materials of the formula (II) have hitherto not beendisclosed and, as novel substances, also form part of the subject-matterof the present application.

They are obtained (process c) when carboxylic acids of the generalformula (V)

in which

L¹, L², L³, L⁴ and Z are as defined above

are reacted with a halogenating agent, if appropriate in the presence ofa diluent and if appropriate in the presence of a catalyst.

The formula (V) provides a general definition of the carboxylic acidsrequired as starting materials for carrying out the process c) accordingto the invention. In this formula (V), L¹, L², L³, L⁴ and Z preferablyor in particular have those meanings which have already been mentionedin connection with the description of the compounds of the formula (I)according to the invention as being preferred or as being particularlypreferred for L¹, L², L³, L⁴ and Z.

The starting materials of the formula (V) have hitherto not beendisclosed and, as novel substances, also from part of the subject-matterof the present application.

They are obtained (process d) when carboxylic acid esters of the generalformula (VI)

in which

L¹, L², L³, L⁴ and Z have the meanings given above and

Alk represents alkyl

are reacted with an acid, if appropriate in the presence of a diluentand if appropriate in the presence of a catalyst.

The formula (VI) provides a general definition of the carboxylic acidesters required as starting materials for carrying out the process d)according to the invention. In this formula (VI), L¹, L², L³, L⁴ and Zpreferably or in particular have those meanings which have already beenmentioned in connection with the description of the compounds of theformula (I) according to the invention as being preferred or as beingparticularly preferred for L¹, L², L³, L⁴ and Z. Alk represents alkyl,preferably methyl or ethyl.

The starting materials of the formula (VI) have hitherto not beendisclosed and, as novel substances, also form part of the subject-matterof the present application.

The starting materials of formula (VI) can be obtained (process e) byreacting 2-(2-hydroxy-phenyl)-2-alkoxyiminoacetic esters of the generalformula (VII)

in which

Alk, L¹, L², L³ and L⁴ are as defined above with a fluoropyrimidine ofthe general formula (VIII)

in which

Z is as defined above and

X³ represents halogen,

if appropriate in the presence of a diluent, such as, for example,acetonitrile, if appropriate in the presence of an acid acceptor, suchas, for example, calcium carbonate.

The formula (VII) provides a general definition of the2-(2-alkoxy-phenyl)-2-methoxyiminoacetic esters required as startingmaterials for carrying out the process e). In this formula (VII), Alk,L¹, L², L³ and L⁴ preferably or in particular have those meanings whichhave already been mentioned in connection with the description of thecompounds of the formula (VI) according to the invention as beingpreferred or as being particularly preferred for Alk, L¹, L², L³ and L⁴.

The starting materials of formula (VII) are known and can be prepared byknown processes (compare, for example, WO-A 94-05626, GB-A 2249092)

The formula (VIII) provides a general definition of thefluoropyrimidines further required as starting materials for carryingout the process e). In this formula (VEII) Z preferably or in particularhas that meaning which has already been mentioned in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred or as being particularly preferred for Z.X³ represents halogen, preferably fluorine or chlorine.

The starting materials of the formula (Vffl) are known and/or can beprepared by known methods (compare, for example, DE 19737723; Chem.Ber., 90<1957>942, 951).

Suitable halogenating agents for carrying out the process c) accordingto the invention are all reagents capable of exchanging hydroxyl groupsattached on carbon for halogens. Examples which may be mentioned are:phosgene, oxalyl chloride, phosphorus trichloride, phosphorustribromide, phosphorus pentachloride, phosphorus oxychloride, thionylchloride or thionyl bromide. The halogenating agents are known chemicalsfor synthesis.

The formula (III) provides a general definition of the hydroxylaminederivatives furthermore required as starting materials for carrying outthe process a) according to the invention. In this formula (III), R¹ andR² preferably or in particular have those meanings which have alreadybeen mentioned in connection with the description of the compounds ofthe formula (I) according to the invention as being preferred or asbeing particularly preferred for R¹ and R².

The starting materials of the formula (HI) are generally customarychemicals for synthesis.

The hydroxamic acid derivatives of the general formula (I) where R² ishydrogen, which hydroxamic acid derivatives are required as startingmaterials for carrying out the process b) according to the invention,are compounds according to the invention and can be prepared by processa).

The formula (IV) provides a general definition of the halogen compoundsfurthermore required as starting materials for carrying out process a)according to the invention. In this formula (IV) R² preferably or inparticular has those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred or as being particularlypreferred for R². X² represents halogen, preferably chlorine.

The starting materials of the formula (IV) are generally customarychemicals for synthesis.

Suitable diluents for carrying out the processes a) and b) according tothe invention are all inert organic solvents. These include, by way ofexample and by way of preference, ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisol;nitrites, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; sulfoxides, such as dimethyl sulfoxide;or sulfones, such as sulfolane.

The processes a) and b) according to the invention are, if appropriate,carried out in the presence of a suitable acid acceptor. Suitable acidacceptors are all customary inorganic or organic bases. These include,by way of example and by way of preference, alkaline earth metal oralkali metal hydrides, hydroxides, amides, alkoxides, acetates,carbonates or bicarbonates, such as, for example, sodium hydride, sodiumamide, sodium methoxide, sodium ethoxide, potassium tert-butoxide,sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodiumacetate, potassium acetate, calcium acetate, ammonium acetate, sodiumcarbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate or ammonium carbonate, and also tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the processes a) and b) according to the invention thereaction temperatures can be varied within a relatively wide range. Ingeneral, the processes are carried out at temperatures from −20° C. to100° C., preferably temperatures from −10° C. to 80° C.

For carrying out the process a) according to the invention for preparingthe compounds of the formula (I), in general from 0.5 to 15 mol,preferably from 0.8 to 8 mol, of substituted hydroxylamine derivative ofthe formula (III) are employed per mole of the carboxylic acidderivative of the formula (II).

For carrying out the process b) according to the invention for preparingthe compounds of the formula (I), in general from 0.5 to 15 mol,preferably from 0.8 to 8 mol, of a halogen compound of the generalformula (IV) are employed per mole of the hydroxamic acid derivative ofthe formula (I) where R² is hydrogen.

Suitable diluents for carrying out the process c) according to theinvention are all inert organic solvents. These include, by way ofexample and by way of preference, aliphatic, alicyclic or aromatichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline, orhalogenated hydrocarbons, such as, for example, chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichloroethane or trichloroethane.

Suitable catalysts for carrying out the process c) according to theinvention are, for example, pyridine or dimethylformamide.

When carrying out the process c) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures from −10° C. to 100°C., preferably at temperatures from 0° C. to 80° C.

For carrying out the process c) according to the invention for preparingthe compounds of the formula (II), in general from 1 to 15 mol,preferably from 2 to 8 mol, of halogenating agent are employed per moleof the carboxylic acid of the formula (V).

Suitable diluents for carrying out the process d) according to theinvention are all inert organic solvents. These include, by way ofexample and by way of preference, aliphatic, alicyclic or aromatichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline, orhalogenated hydrocarbons, such as, for example, chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichloroethane or trichloroethane.

The process d) according to the invention is, if appropriate, carriedout in the presence of an acid. Suitable acids are all inorganic andorganic protonic acids including, by way of example and by way ofpreference, Lewis acids, and also all polymeric acids. These include,for example, hydrogen chloride, sulfuric acid, phosphoric acid, formicacid, acetic acid, trifluoroacetic acid, methanesulfonic acid,trifluoromethanesulfonic acid, toluenesulfonic acid, boron trifluoride(also as etherate), boron tribromide, aluminum trichloride, titaniumtetrachloride, tetrabutylorthotitanate, zinc chloride, iron (III)chloride, antimony pentachloride, acidic ion exchangers, acidic aluminaand acidic silica gel.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the process is carried out at temperatures from −50° C. to 80° C.,preferably at temperatures from −20° C. to 50° C.

For carrying out the process d) according to the invention for preparingthe compounds of the formula (V), in general from 1 to 15 mol,preferably from 2 to 8 mol, of acid are employed per mole of thecarboxylic acid ester of the formula (VI).

All processes according to the invention are generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure in general between 0.1 bar and 10 bar.

The practice of the reaction and work-up and isolation of the reactionproducts are carried out by generally customary processes (compare alsothe Preparation Examples).

The substances according to the invention have potent microbiocidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or

Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidial form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidial form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae; Pellicularia species, such as, for example, Pelliculariasasakii; Pyricularia species, such as, for example, Pyricularia oryzae;Fusarium species, such as, for example, Fusarium culmorum; Botrytisspecies, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

According to the invention, it is possible to treat all plants and partsof plants. By plants are understood here all plants and plantpopulations such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants can be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant varieties which can or cannot be protected by varietal propertyrights. Parts of plants are to be understood as meaning all above-groundand below-ground parts and organs of plants, such as shoot, leaf, flowerand root, examples which may be mentioned by way of example beingleaves, needles, stems, trunks, flowers, fruit bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment according to the invention of the plants and parts ofplants with the active compounds is carried out directly or by action ontheir environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

The active compounds according to the invention can be employedparticularly successfully for controlling cereal diseases, such as, forexample, against Erisiphe or Puccinia species, diseases in viticultureand fruit and vegetable growing such as, for example, against Venturia,Sphaerotheca, phytophtora and Plasmopara species, or rice diseases, suchas, for example, against Pyricularia species.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents.

Essentially, suitable liquid solvents are: aromatics such as xylene,toluene or alkylnaphthalenes, chlorinated aromatics or chlorinatedaliphatic hydrocarbons such as chlorobenzenes, chloroethylenes ormethylene chloride, aliphatic hydrocarbons such as cyclohexane orparaffins, for example petroleum fractions, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide or dimethyl sulfoxide, or else water.Liquefied gaseous extenders or carriers are to be understood as meaningliquids which are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulfonates, alkyl sulfates, arylsulfonates, or else proteinhydrolysates. Suitable dispersants are: for example lignin-sulfite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivescan be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 percent by weightof active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations, also in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of suitable mixing partners are the following:

Fungicides:

aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulfide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminum, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,ininoctadine triacetate, iodocarb, ipconazole, iprobenfos (DBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulfate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulfur and sulfur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

α-(1,1-dimethylethyl)-C-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,

α-(2,4-dichlorophenyl)-β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,

β-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]1H-1,2,4-triazole-1-ethanol,

(5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

(E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanoneO-(phenylmethyl)-oxime,

1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

1-[(diiodomethyl)-sulfonyl]-4-methyl-benzene,1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol,

2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

2-[(1-methylethyl)-sulfonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,2-aminobutane,

2-bromo-2-(bromomethyl)-pentanedinitrile,

2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

3-(1,1-dimethylpropyl-1-oxo 1H-indene-2-carbonitrile,

3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide,

4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

8-hydroxyquinoline sulfate,

9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

cis4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine

hydrochloride,

ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

potassium hydrogen carbonate,

methanetetrathiol sodium salt,

methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide.

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulfonamide,

N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,

N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline,probenazole, streptomycin, tecloftalam, copper sulfate and other copperpreparations.

Insecticides/Acaricides/Nematicides:

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophosA, bufencarb, buprofezin, butathiofos, butocarboxim, butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, diflubenzuron, dimethoat, dimethylvinphos,diofenolan, disulfoton, docusat-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoat, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoat, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb,pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur, prothiofos,prothoat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben,pyridathion, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, thetacypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI5302

zeta-cypermethrin, zolaprofos

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]

-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-diemthylethyl)phenyl]4,5-dihydro-oxazole,

2-(acetlyoxy)-3-docecyl-1,4-naphthalenedione,

2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

3-methylphenyl propylcarbamate

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

Bacillus thuringiensis strain EG-2348,

[2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)4-pyridazinyl]oxy]ethyl]-carbamate,

N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoranridothioate.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi, for example against Candida species,such as Candida albicans, Candida glabrata such as Epidermophytonfloccosum, Aspergillus species, such as Aspergillus niger andAspergillus fumigatus, Trichophyton species, such as Trichophytonmentagrophytes, Microsporon species such as Microsporon canis andaudouinii. The list of these fungi in no way limits the mycotic spectrumwhich can be covered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

The examples below serve to illustrate the invention. However, theinvention is not limited to the examples.

PREPARATION EXAMPLES Example 1

2-(2-{[6-(2-Chlorophenoxy)-5-fluoro-4-pyrimidinyl)oxy}phenyl)-N-hydroxy-2-methoxyimino)-N-methylacetamide

47.2 g (0.47 mol) of triethylamine are initially added to a mixture of32.45 g (0.39 mol) of N-methylhydroxylamine hydrochloride in 400 ml oftetrahydrofuran, the mixture is cooled to 0° C., and at thistemperature, a solution of 33.6 g (0.078 mol) of2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetylchloride in 50 ml of tetrahydrofuran is then added dropwise over aperiod of 1 hour. Without further cooling, stirring is continued for 18hours. The reaction mixture is poured into 2 l of water and extracted 3times with in each case 400 ml of ethyl acetate. The combined organicphases are dried over sodium sulfate and concentrated under reducedpressure. The residue is stirred with diisopropyl ether, filtered offwith suction and dried. This gives 13.2 g (38% of theory) of2-(2-{[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-N-hydroxy-2-(methoxyimino)-N-methylacetamide.

HPLC: logP=2.82

Example 2

2-(2-{[6-(2-Chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-N-hydroxy-2-(methoxyimino)-acetamide

1.4 g (0.014 mol) of triethylamine are initially added to a mixture of0.8 g (0.012 mol) of hydroxylamine hydrochloride in 20 ml oftetrahydrofuran, the mixture is cooled to 0° C., and at thistemperature, a solution of 1 g (0.0023 mol) of2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetylchloride in 10 ml of tetrahydrofuran is then added dropwise. Withoutfurther cooling, stirring is continued for 18 hours. The reactionmixture is poured into 100 ml of 1 N hydrochloric acid and extracted 3times with in each case 100 ml of ethyl acetate. The combined organicphases are dried over sodium sulfate and concentrated under reducedpressure. The residue is chromatographed on silica gel usingcyclohexane/ethyl acetate (4:1). This gives 0.3 g (30% of theory) of2-(2-{[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-N-hydroxy-2-(methoxyimino)-acetamide.

HPLC: logP=2.56

Example 3

N-(Acetyloxy)-2-(2-{[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide

0.12 g (0.0012 mol) of triethylamine is initially added to a mixture of0.4 g (0.0009 mol) of2-(2-{[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-N-hydroxy-2-(methoxyimino)-N-methylacetamidein 20 ml of tetrahydrofuran, and 0.08 g (0.00099 mol) of acetyl chlorideis then added and the mixture is stirred at room temperature for 1 hour.The reaction mixture is poured into 100 ml of water and extracted 3times with in each case 50 ml of ethyl acetate. The combined organicphases are dried over magnesium sulfate and concentrated under reducedpressure. The residue is chromatographed on silica gel usingcyclohexane/ethyl acetate (4:1). This gives 0.18 g (41.1% of theory) ofN-(acetyloxy)-2-(2-{[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide.

HPLC: logP=3.52

The compounds of the formula (Ia) listed in Table 1 below are likewiseobtained analogously to Examples 1 to 3, and in accordance with thedetails given in the general descriptions of processes a) and b).

TABLE 1 (Ia)

Example Z R¹ R² log P 4 2-fluorophenyl —CH₃ —H 2.66 53-chloro-2-methylphenyl —CH₃ —H 3.29 6 2,5-dichlorophenyl —CH₃ —H 3.28 72,3-dichlorophenyl —CH₃ —H 3.22 8 2-cyanophenyl —CH₃ —H 2.43 92-chlorophenyl —CH₃ —CH₃ 3.5 **) The log P values were determined inaccordance with EEC directive 79/831 Annex V. A8 by HPLC (gradientmethod, acetonitrile/0.1% aqueous phosphoric acid)

Preparation of the Precursors Example (II-1)

2{2-[6-(2-Chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl)}-2-methoxyimino-acetylchloride

50 mg of dimethylformamide are initially added to a solution of 10 g(0.024 mol) of2-({2-[6-(2-chlorophenoxy)-5-fluoro-pyriimidin-4-yloxy]-phenyl)}-2-methoxyiminoaceticacid in 200 ml of dichloromethane, and 3.95 g (0.031 mol) of oxalylchloride are then added dropwise. Stirring is continued at 40° C. for 5hours and then without further input of heat for 18 hours. The reactionmixture is concentrated under reduced pressure. This gives 10.4 g (99.6%of theory) of2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetylchloride.

Example (V-1)

2-1{2-[6-(2-Chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoaceticacid

At −10° C., 46.4 ml (0.046 mol) of boron tribromide are added dropwiseto a solution of 4 g (0.0093 mol) of methyl2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetatein 40 ml of dichloromethane, and the mixture is warmed to roomtemperature over a period of 1 hour and stirred for another 2 hours.With cooling, 300 ml of water are added dropwise, and the organic phaseis then separated off. The aqueous phase is extracted two more timeswith in each case 100 ml of dichloromethane. The combined organic phasesare filtered through kieselguhr, dried over magnesium sulfate andconcentrated under reduced pressure. This gives 3.8 g (98.3% of theory)of2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoaceticacid.

NMR ([DMSO, TMS): δ=3.83 (s), 7.34-7.67 (m), 8.13 (s), 13.38 (s)

Example (VI-1)

Methyl2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetate

40 g (0.29 mol) of ground potassium carbonate and 58 g (0.24 mol) of4-(2-chlorophenoxy)-5,6-difluoropyrimidine are added to a solution of 50g (0.24 mol) of methyl 2-(2-hydroxyphenyl)-2-methoxyiminoacetate in 600ml of acetonitrile, and the mixture is stirred at 25° C. for 18 hours.The reaction mixture is poured into 3 l of ice-water and the resultingsolid is filtered off with suction. This gives 102 g (98.7% of theory)of methyl2-{2-[6-(2-chlorophenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}-2-methoxyiminoacetate.

HPLC: logP=3.61

USE EXAMPLES Example A

Puccinia Test (wheat)/protective

Solvent: 25 parts by weight of N,N-dimethylacetamide Emulsifier: 0.6part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Puccinia recondita. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of 80% to promote the developmentof rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to the control, whereas an efficacy of 100%means that no infection is observed.

In this test, the substances according to the invention mentioned inExamples (1), (4), (8) exhibit an efficacy of 95% or more at anapplication rate of 125 g/ha.

Example B

Phytophthora Test (Tomato)/Protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1.0 part by weight of alkyl-arylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Phytophthora infestans. The plants are then placedin an incubation cabin at about 20° C. and 100% relative atmospherichumidity.

Evaluation is carried out 3 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention mentioned inExamples (1), (5), (7) exhibit an efficacy of 86% or more at anapplication rate of 100 g/ha.

Example C

Plasmopara Test (Grapevine)/Protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabin at about 20° C. and 100% relative atmospheric humidity for 1 day.The plants are then placed in a greenhouse at about 21° C. and about 90%relative atmospheric humidity for 5 days. The plants are then moistenedand placed in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention mentioned inExamples (1), (5), (7) exhibit an efficacy of 95% or more at anapplication rate of 100 g/ha.

Example D

Sphaerotheca Test (Cucumber)/Protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycolether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are then placedin a greenhouse at about 23° C. and a relative atmospheric humidity ofabout 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention mentioned inExamples (1), (5), (7) exhibit an efficacy of 95% or more at anapplication rate of 100 g/ha.

Example E

Venturia Test (Apple)/Protective

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier: 1.0 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention mentioned inExamples (1), (5) (7) exhibit an efficacy of 96% or more at anapplication rate 10 of g/ha.

Example F

Pyricularia Test (Rice)/Protective

Solvent: 25 parts by weight of N,N-dimethylacetamide Emulsifier: 0.6part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young rice plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Pyricularia oryzae and then remain at 100% rel.atmospheric humidity and 26° C. for 24 h. The plants are then placed ina greenhouse at 80% rel. atmospheric humidity and a temperature of 26°C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention mentioned inExamples (1), (4) (5), (7) exhibit an efficacy of 90% or more at anapplication rate of 250 g/ha.

Example G

Erysiphe Test (Barley)/Protective

Solvent: 50 parts by weight of N,N-dimethylformamide Emulsifier: 1.2parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, and theconcentrate is diluted with water and emulsifier to the desiredconcentration.

To test for protective activity, young cereal plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with spores of Erysiphegraminis f. sp. hordei. The plants are then placed in a greenhouse at70% relative atmospheric humidity and a temperature of 18° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

In this test, the substances according to the invention mentioned inExamples (1), (5), (7) exhibit an efficacy of 80% or more at anapplication rate of 750 g/ha.

What is claimed is:
 1. A compound of the Formula (I)

wherein Z represents in each case substituted or unsubstitutedcyoloalkyl or aryl or represents furyl, pyridyl or thienyl which isoptionally substituted by methyl or thenyl, L¹, L², L³ and L⁴ areidentical or different and independently of one another each representhydrogen, halogen, cyano, nitro, in each case optionallyhalogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl oralkylsulfonyl, R¹ represents hydrogen or alkyl and R² representshydrogen, alkyl, alkylcarbonyl, alkoxycarbonyl or arylcarbonyl.
 2. Acompound of the Formula (I) as claimed in claim 1, wherein Z representscycloalkyl having 3 to 7 carbon atoms which is optionally mono- todisubstituted by halogen, alkyl or hydroxyl; or represents phenyl ornaphthyl, each of which is optionally mono- to tetrasubstituted byidentical or different substituents, where the optional substituents areselected from the group consisting of: halogen, cyano, nitro, amino,hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; in each casestraight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy,alkoxyalkyl, alkylthloalkyl, dialkoxyalkyl, alkylthio, alkylsulfinyl oralkyfsulfonyl having in each case 1 to 8 carbon atoms; in each casestraight-chain or branched alkenyl or alkenyloxy having in each case 2to 6 carbon atoms; in each case straight-chain or branchedhalogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulfinylor halogenoalkylsulfonyl having in each case 1 to 6 carbon atoms and 1to 13 identical or different halogen atoms; in each case straight-chainor branched halogenoalkenyl or halogenoalkenyloxy having in each case 2to 6 carbon atoms and 1 to 11 identical or different halogen atoms; ineach case straight-chain or branched alkylamino, dialkylamino,alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy,alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in thehydrocarbon chains; cycloalkyl or cycloalkyloxy having in each case 3 to6 carbon atoms; in each case doubly attached alkylene having 3 to 4carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylenehaving 1 or 2 carbon atoms, each of which is optionally mono- totetrasubstituted by identical or different radicals selected from thegroup consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl andethyl; a grouping

 in which A¹ represents hydrogen, hydroxyl or alkyl having 1 to 4 carbonatoms or cycloalkyl having 1 to 6 carbon atoms and A² representshydroxyl, amino, methylamino, phenyl, benzyl or represents in each caseoptionally cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino,dialkylamino- or phenyl-substituted alkyl or alkoxy having 1 to 4 carbonatoms, or represents alkenyloxy or alkinyloxy having in each case 2 to 4carbon atoms, and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl,cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio,or heterocyclyalkyl, having in each case 1 to 3 carbon atoms in thealkyl moieties in question, each of which radicals is optionally mono-to trisubstituted in the cyclic moiety by halogen and/or straight-chainor branched alkyl or alkoxy having 1 to 4 carbon atoms, L¹, L², L³ andL⁴ are identical or different and independently of one another eachrepresent hydrogen, halogen, cyano, nitro, or alkyl, alkoxy, alkylthio,alkylsulfinyl or alkylsulfonyl having in each case 1 to 6 carbon atoms,each of which is optionally substituted by 1 to 5 halogen atoms, R¹represents hydrogen or alkyl and R² represents hydrogen, alkyl,alkylcarbonyl, alkoxycarbonyl or arylcarbonyl.
 3. A compound of theFormula (I) as claimed in claim 1, wherein Z represents cyclopentyl orcyclohexyl, each of which is optionally mono- to disubstituted byfluorine, chlorine, methyl, ethyl or hydroxyl; represents furyl, pyridylor thienyl which is optionally substituted by methyl or ethyl; orrepresents phenyl or naphthyl, each of which is optionally mono- totetrasubstituted by identical or different substituents, where theoptional substituents are selected from the group consisting of:fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl,formyl, carboxyl, carbamoyl), thiocarbamoyl, methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, neo-pentyl, 1-, 2-, 3-,4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 4,5-(2-methylpentyl),1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-, 3-, 4-(2,2-dimethylbutyl),1-, 2-(2,3-dimethylbutyl), hydroxymethyl, hydroxyethyl, 3-oxobutyl,methoxymethyl, dimethoxymethyl, methoxy, ethoxy, n or i-propoxy,methoxymethyl, ethoxymethyl, methylthio, ethylthio, n- or i-propylthio,methylsulfinyl, othylsulfinyl, methylsuffonyl or ethylsulfonyl,methylthiomethyl, ethykthiomethyl, vinyl, allyl, 2-methylallyl,propen-1-yl, crotonyl, propargyl, vinyloxy, allyloxy, 2-methylallyloxy,propen-1-yloxy, crotonyloxy, propargyloxy; trifluoromethyl,trifluoroethyl, diffluoromethoxy, trifluoromethoxy,difluorochloromethoxy, trifluoroethoxy, difluoromethylthio,trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinylor trifluoromethyl-sulfonyl, methylamino, ethylamino, n- ori-propylamino, dimethylamino, diethyl-amino, acetyl, propionyl,methoxycarbonyl, ethoxycarbonyl, methylamino-carbonyl,ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylaminocarbonyl,acryloyl, propioloyl, cyclopentyl, cyclohexyl, in each case doublyattached propanediyl, ethyleneoxy, methylenedioxy, ethylenedioxy, eachof which is optionally mono- to tetrasubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,oxo, methyl and trifluoromethyl a grouping

 where A¹ represents hydrogen, methyl or hydroxyl and A² representshydroxyl, methoxy, ethoxy, amino, methylamino, phenyl, benzyl orhydroxyethyl, and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl,cinnamoyl, benzyl, phenylethyl, phenylpropyl, benzyloxy, benzylthio,5,6-dihydro-1,4,2-dioxazin-3ylmethyl, triazolylmethyl,benzoxazol-2-ylmethyl, 1,3-dioxan-2-yl, benzimidazol-2-yl, dioxol-2-yl,oxadiazoly, each of which is optionally mono- to trisubstututed in thecyclic moiety by halogen and/or straight-chain or branched alkyl oralkoxy having 1 to 4 carbon atoms, L¹, L², L³ and L⁴ are identical ordifferent and independently of one another each represents hydrogen,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, R¹ representshydrogen or alkyl, R² represents hydrogen, alkyl, alkylcarbonyl,alkoxycarbonyl or arylcarbonyl.
 4. A compound of the Formula (I) asclaimed in claim 1, wherein Z represents phenyl which is in each caseoptionally mono- to trisubstituted by identical or differentsubstituents, where the substituents are selected from the groupconsisting of fluorine, chlorine, C₁-C₄-alkyl and cyano, L¹, L², L³ andL⁴ represent hydrogen, R¹ represents C₁-C₄-alkyl, and R² representshydrogen or methyl.
 5. A compound of the Formula (II)

wherein Z, L¹, L², L³ and L⁴ are as defined in claim 1 and X¹ representshalogen.
 6. A compound of the Formula (V)

wherein L¹, L², L³, L⁴ and Z are as defined in claim
 1. 7. A compound ofthe Formula (VI)

wherein L¹, L², L³, L⁴ and Z are as defined in claim 1 and Alkrepresents alkyl.
 8. A process for preparing a compound of the Formula(I), as defined in claim 1, comprising a step selected from the groupconsisting of step (a) and step (b), wherein a) said step (a), comprisesthe step of reacting a carboxylic acid derivative of the Formula (II)

wherein L¹, L², L³, L⁴ and Z are as defined in claim 1 and X¹ representshalogen, with a substituted or unsubstituted hydroxylamine derivativesof the Formula (III)

wherein R¹ and R² are as defined in claim 1, optionally in the presenceof a diluent and optionally in the presence of an acid acceptor, and b)said step (b) comprises the step of reacting a compound of the Formula(I) according to claim 1, where R² is hydrogen with a halogen compoundof the Formula (IV) X²—R²′  (IV) wherein R²′ represents alkyl,alkylcarbonyl, alkoxycarbonyl or arylcarbonyl and X² represents halogen,optionally in the presence of a diluent, optionally in the presence ofan acid acceptor.
 9. A composition comprising at (east one compound ofthe Formula (I) according to claim 1 and one or more extenders and/orcarriers and optionally, one or more surfactants.
 10. A method forcontrolling pests, comprising the step of applying a member selectedfrom the group consisting of an effective amount of a compound asdefined in claim 1 and an effective amount of a composition as definedin claim 9 to a member selected from the group consisting of said pests,a habitat of said pests, and combinations thereof.
 11. A process forpreparing a pesticide comprising the step of mixing a compound of theFormula (I) as defined in claim 1 with one or more extenders and/or oneor more surfactants.